Synthesis and antiallergic activity of some quinolinones and imidazoquinolinones

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Abstract
A group of 1,4-dihydro-4-oxoquinoline-2- and -3-carboxylic acid esters with N functionality at the 8-position was synthesized, and 6-oxo-6H-imidazo[4,5,1-ij]quinoline-4- and -5-carboxylic acid esters were elaborated from these. Several of the compounds displayed activity in the rat passive cutaneous anaphylaxis (PCA) test for antiallergic activity [1,4-dihydro-8-nitro-4-oxo-2-quinolinecarboxylic acid methyl ester, 6-oxo-6H-imidazo[4,5,1-ij]quinoline 4-carboxylic acid methyl ester, 8-[(1-ethoxyethylidene)amino]-1,4-dihydro-4-oxo-2-quinolinecarboxylic acid methyl ester, 1,4-dihydro-8-nitro-4-oxo-3-quinolinecarboxylic acid ethyl ester, 8-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethylester, 6-oxo-6H-imidazo[4,5,1-ij]quinoline-5-carboxylic acid ethyl ester, 2-methyl-6-oxo-6H-imidazo[4,5-1-ij]quinoline-5-carboxylic acid ethyl ester, 8-(formylamino)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 8-(formylamino)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester]. PCA activity in this series was accompanied by rat toxicity, as measured by a decrease in percent of normal weight gain over a 2 wk period, following a single oral dose.